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Synthesis 2020; 52(15): 2190-2195
DOI: 10.1055/s-0040-1708017
DOI: 10.1055/s-0040-1708017
paper
Three-Component Reaction of Homophthalic Anhydride with Carbonyl Compounds and Ammonium Acetate: New Developments
This research was supported by the Russian Foundation for Basic Research (project grant 18-33-00016). Alexander Safrygin is grateful to Saint Petersburg State University for providing his postdoctoral fellowship.Further Information
Publication History
Received: 05 March 2020
Accepted after revision: 26 March 2020
Publication Date:
16 April 2020 (online)
Abstract
The earlier described reaction of homophthalic anhydrides with aromatic ketones and ammonium acetate was tested for cyclic ketones (yielding spirocyclic motifs) and aliphatic aldehydes. In contrast to previous findings, the reaction was found to require no catalyst at all and to be applicable, in the non-catalyzed format, to these new carbonyl substrates as well as aromatic ketones. The reaction typically proceeds with high diastereoselectivity; if not, the initial diastereomeric mixture can be quantitatively equilibrated into a single, trans-diastereomer on treatment with aqueous base.
Key words
Castagnoli–Cushman reaction - homophthalic anhydride - tetrahydroisoquinolonic acids - catalyst-free - spirocyclic compounds - diastereoselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1708017.
- Supporting Information
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